Allyl bromide → ((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester

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Reaction Steps

To a suspension of 0.28 g (6.44 mmol) sodium hydride in 40 ml dimethylformamide were added at 0° C. 2.0 g (6.44 mmol) ((6R,7S)-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester in 20 ml dimethylformamide. After 30 minutes 0.55 ml (6.44 mmol) allyl bromide was added. Stirring was continued for 3 hours. Extraction with ethylacetate/water and chromatography on silicagel with heptane to ethylacetate/heptane 1:1 yielded 2.24 g (99%) ((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester, MS m/e (%): 351.2 (M+H+, 80), 295.3 (100), 251.1 (82).

Provenance & Evidence